Polyolefin fiber dyeing with an arylazo 8-hydroxy-quinoline-5-sulfonic acid and fibers so dyed

ABSTRACT

THE COLORATION OF FIBERS OF ALPHA OLEFIN POLYMERS CONTAINING METALS, WITH A PHENYLAZO-8-HYDROXYQUINOLINE-5SULFONATE WITH OR WITHOUT A 6-METHYL GROUP IN THE QUINOLINE RADICAL. THE PHENYL GROUP MAY BE SUBSTITUTED BY HALOGEN, METHYL, ALKOXY, NITRO OR CYANO GROUPS. THE FIBERS ARE EXEMPLIFIED WITH POLYPROPYLENE WITH NICKEL SALTS.

United States Patent Int. Cl. D 06p 1/02 and Joseph assignors to UgineKuhl- U.S. Cl. 8-42 8 Claims ABSTRACT OF THE DISCLOSURE The colorationof fibers of alpha olefin polymers containing metals, with aphenylazo-8-hydroxyquinoline-5- sulfonate with or without a G-methylgroup in the quinoline radical. The phenyl group may be substituted byhalogen, methyl, alkoxy, nitro or cyano groups. The fibers areexemplified with polypropylene with nickel salts.

The present application is a continuation-in-part of applicantscopending parent application Ser. No. 455,298 filed May 12, 1965.

The present invention concerns a process for the coloration ofalpha-olefin polymers.

It is diflicult to obtain colorations on synthetic fibers based onpolymers of alpha-olefin such as polypropylene which are fast to lightand to dry cleaning with chlorinated solvents. It has been proposed toremove this drawback by incorporating metals such as nickel, chromium,cobalt, or aluminium, which enable metallisable or lakeable' dyestulfsto be fixed firmly on the fibers.

French Pat. No. 1,320,986 of Mar. 2, 1962, describes the coloration ofpolypropylene fibers containing metals of Groups Ila, IIb or IVb of thePeriodic Table, i.e. magnesium. calcium, strontium, barium, cadmium,zinc, tin or lead. excluding metals of other groups, e.g. nickel,cobalt, chromium or aluminium, with dyestuffs belonging to the arylazo8-hydroxy-quinoline series.

The present invention relates to the application of the dyeing of fibersbased on alpha-olefin polymers, such as polypropylene, containingmetals, especially nickel, of dyestuffs of the general formula:

in which X represents hydrogen or methyl and R and R each representhydrogen, halogen, methyl, alkoxy, nitro or cyano.

Compared with analogous unsulphonated dyestuffs, the dyestuffs which maybe used according to the invention in many cases show a better affinityfor the fiber espe-' cially in the case of very deep shades. They aresuitable for the coloration of fibers in whatever form they may bepresent, e.g. wadding, carded material, yarn or fabric. They may be usedin dyeing or printing, according to the various known industrialtechniques, such as dyeing in an open bath, with a circulatingapparatus, in a vat or jig, and dyeing by foularding. Further, thesedyestuffs have the advantage that they may be applied at 90l00 C.without the addition of a vehicle. In spite of the solubility which thesulphonic group confers on the dyestulfs, it is advantageous to applythem in a dispersed form.

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The following examples, in which the parts are parts by weight, aregiven without the invention being limited thereto:

EXAMPLE 1 25 parts of polypropylene fibers containing nickel wereintroduced into a dyebath comprising 1000 parts of water, one part 'ofthe product resulting from the condensation of one mole of caster oilwith 40 moles of ethylene oxide, one part of acetic or formic acid and aquantity of dispersed dyestuff corresponding to 0.25 to 1 part of a puredyestufi prepared by coupling one mole of the diazo derivative of 4nitro 2 cyano aniline with one mole of 6-methyl8-hydroxy-quinoline-S-sulphonic acid. The bath was heated to boiling andkept at the boil for 2 hours. The fiber s were rinsed and stripped in analkaline reducing bath. A navy blue shade was obtained which possessedgood fastness to light and an excellent fastness to the chlorinatedsolvents used in dry cleaning.

EXAMPLE 2 25 parts of polypropylene fibers containing nickel wereintroduced into a dyebath analogous to that of Example 1, containing aquantity of dispersed dyestuff corresponding to 0.25 to 1 part of a puredyestutf prepared by coupling one mole of the diazo derivative of4-nitro-2-cyano-aniline with one mole of 8-hydroxy-quinoline-5-sulphonicacid. The bath was heated to boiling and maintained at the boil for 2hours. The fibers were rinsed and stripped in an alkaline reducingmedium. A navy blue shade with very good fastness to light and anexcellent fastness to the chlorinated solvents used in dry cleaning wasobtained.

When this dyestuff was compared with the corresponding unsulphonatedone, a fall of the tinctorial yield for a light shade was observed; onthe other hand, the tinctorial yield was superior for a dark shade.

EXAMPLE 3 ing to 0.25 to 1 part of a pure dyestufi prepared by couplingone mole of the diazo derivative of 2,4-dinitr0- aniline with one moleof 6-methyl-8-hydroxy-quinoline-5- sulphonic acid. The bath was heatedto boiling and kept at the boil for 2 hours. The fibers were rinsed andstripped in an alkaline reducing medium. A navy blue shade was obtainedwith good fastness to light and excellent fastness to the chlorinatedsolvents used in dry cleaning.

EXAMPLE 4 25 parts of polypropylene fibers containing nickel wereintroduced into a dyebath analogous to that of Example 1, but containinga quantity of dispersed dyestufl? corresponding to 0.25 to 1 part of apure dyestuff prepared by coupling one mole of 4-nitro-2-chloro-anilinewith one mole of 6-methyl-8-hydroxy-quinoline-5-sulphonic acid. The bathwas heated to boiling and kept at the boil for 2 hours. The fibers wererinsed and stripped in an alkaline reducing medium. A dark bordeauxshade was obtained with good fastness to light and excellent fastness tothe chlorinated solvents used in dry cleaning.

EXAMPLE 5 C. The fabric was vigorously washed in a bath of soap andsodium carbonate at the boil and stripped in an alkaline reducing bath.A navy blue shade was obtained which possessed excellent fastness to thechlorinated solvents used in dry cleaning and good fastness to light.

In the foregoing examples it is understood that the term stripped merelymeans that the excess or unfixed dye- 4 4. Process according to claim 1wherein the dyestuff is applied in dispersed form.

5. Process according to claim 1 wherein the coloration is effected bydyeing in an open bath at a temperature of 5 90 C. to 100 C.

6. Fibers based on a polymer of an alpha-olefin containing a metalcolored by a dyestufi? of the general forstuff is removed. mula' R 011 Rl EXAMPLES 6 TO 11 j On replacing the dyestuff used in Examples 1 and 5by the dyestuffs enumerated in the table below, shades were obtainedwith similar properties. 0311 TABLE I Dyestufi derived lron1 Shade onpolypropylene fibers containing Diazotized base Coupling compound nickelExample:

6 2,5-dichloro-anil1ne 6-methyl-S-hydroxy-quinoline-5'sulphonic acidRed. 7 3,4 dirnethylaniline do Orange. 8. 4-nitro-aniline "do Bordeaux.9. 4-chloro-aniline do.. Orange. 10 3-metl1oxy-aniline .do Do. 114-nitro-2-chloro-aniline 8-l1ydroxy-quinoline-Ssulphonic acid Violet.

We claim: wherein X represents a member selected from the group 1.Process for the coloration of fibers based on a polymer of analpha-olefin containing a metal which comprises applying thereto adyestuif of the general formula:

is polypropylene.

3. Process according to claim 1 wherein the metal is nickel.

polypropylene. 0

consisting of hydrogen and methyl, and R and R each represent a memberselected from the group consisting of hydrogen and halogen atoms,methyl, alkoxy, nitro, and cyano groups.

7. Fibers according to claim 6 wherein the metal is nickel.

8. Fibers according to claim 7 wherein the polymer is References CitedFOREIGN PATENTS 642,346 5/1964 Belgium 8-42 40 DONALD LEVY, PrimaryExaminer US. Cl. X.R.

